Pros and Cons of Going Into Business With Your BFF

A look at some of the pros and cons of working with your BFF: from bringing a new depth to brainstorm sessions to compartmentalizing relationship issues.

Entrepreneurship can be a difficult, lonely road. It’s no wonder many consider embarking on that journey with their best friend. Still, we’ve all heard the horror stories, right? The tales of inseparable friendships turned sour because of business.

By its nature, business decisions must be made from an impersonal standpoint. That’s pretty difficult when friends are involved. And it explains why Harvard Business School revealed that among technology startups, the ones founded by friends were the most unstable. This, combined with the 90% failure rate of startups, is pretty disheartening. Statistically speaking, you’re probably better off ignoring your friend’s proposition to build a business with you.

But I’m not the kind of gal that follows statistics. In fact, last year I partnered with my best friend to take my freelance business to the next level. The result? A six-figure company where I get to spend time laughing, brainstorming and building something great with one of the most important people in my life. Today, I’ll take you through some of the pros and cons I’ve experienced in the past 18 months of working with my BFF.

Pro: Brainstorming Sessions Enter a New Realm

Brainstorming works best when you can let go of your expectations and really allow your creative juices to flow. Because I’m so comfortable around my best friend, this isn’t difficult. In normal brainstorming sessions, I get a bit self-conscious about the quality of each idea. But with my best friend, those kinds of inhibitions don’t hinder me.

I’ve found that this brings new depth to brainstorm sessions. Ideas can come and go, we build with one another and, ultimately, better ideas are born.

Con: It’s Hard to Distinguish Between Work and Play

Sometimes my best friend comes come over to work but we end up chatting and hanging out most of the time she’s here. If either of you are working on an hourly basis, it can become really hard to distinguish what qualifies as work and what’s just hanging out with your bestie.

On the flip side, there have also been times where we’ve been on the phone, only to end up brainstorming about something business-related. Or I’ll have a bright idea at 10pm and want to call her.

Outside of time-tracking, this is also an issue of boundaries. It’s important to talk about when it’s okay to talk business and when it’s not. I’m much more of a workaholic than my BFF, so I try to be conscious of only talking business when it’s appropriate. There have been times, for example, where she’ll ask me to go to lunch with the qualifier, “But no talking business.” These types of boundaries bring balance to our friendship.

Pro: You Have Someone to Bear Your Burdens

Venturing into entrepreneurship is a huge undertaking. Instead of just showing up for work 8-hours a day, you now have to worry about every aspect of the business. As someone that has tried to do this alone, trust me, it gets heavy.

Having my best friend with me in business takes some of this load off. She’s there with me when I’m celebrating a new contract, and she shares the stress when I lose a client.

Con: You Must Compartmentalize Relationship Issues

BFFs fight. It just happens. And sometimes things can get a bit out of hand (e.g. yelling, door slamming or even the silent treatment). While not talking for a week or so gives space for things to blow over with your BFF, the same tactic doesn’t translate to business. If you’re not careful, you could put the business in a precarious situation.

Disagreements happen, both in business and friendships. But how you handle arguments has to be different in each situation. Where BFFs can sometimes get away with more irrational behavior, business partners must know how to discuss disagreements in a calm, logical manner.

You need to learn how to compartmentalize your personal issues with each other: Being at odds with your BFF can’t automatically mean being at odds with your business partner.

Learning this balance is difficult, but it’s necessary if you want to succeed together.

Pro: They Accept Your Strengths and Weaknesses

It’s a wonderful thing to have someone who accepts you. Your BFF is someone who knows some of the most personal things about you, and they choose to be your friend with full knowledge of your baggage as well as your amazing attributes.

This type of knowledge and understanding can go a long way in business, just as it does in friendship. Lose a big account? Feeling inadequate? Your best friend can make you feel encouraged and supported. But you can also trust them to be forthright about your strengths and weaknesses, unpack what you did right or wrong and then help you develop a plan to move onwards and upwards.

Con: Performance Issues Are Awkward to Address

If an employee is slacking, having a conversation about productivity is pretty straightforward: You sit down, conduct a review and outline steps to rectify the behavior. It can be more difficult to have this kind of conversation with your bestie; the last thing you want is to cause hurt or make them feel inadequate.

With besties, you can be nearly too empathetic; for example, knowing what’s going on in your bestie’s personal life might make you inclined to forgive behaviour you wouldn’t tolerate in a straightforward business relationship.

When you encounter these situations, it’s important to realize that your friend is probably feeling similar awkwardness. Having a high level conversation about how you can both handle these types of conversations will help reduce the awkwardness when the need arises.

Remember that everything is more personal when you’re working with your best friend. While that comes with many advantages, it also means making a special effort to navigate the complex duality of your relationships — definitely something to keep in mind before you partner up.


Ultimately, you need to make the decision that’s right for you and your BFF. If you’re going to move forward as business partners, it’s important to always put the friendship first. Keep the lines of communication open, and always tackle problems head on; there’s no room for hiding your feelings and being passive aggressive.

Time will tell if my BFF and I will make it for the long haul, but for now I’m really enjoying the experience. Are you planning to go into business with your best friend? If so, I’d love to chat with you about it in the comments below!

about the author

Freelance Contributor Chelsei Henderson is a content marketing consultant helping freelancers and entrepreneurs build successful companies in the digital world.